diff --git a/backend/src/__tests__/objUtils.spec.ts b/backend/src/__tests__/objUtils.spec.ts
new file mode 100644
index 0000000000..6915693a3b
--- /dev/null
+++ b/backend/src/__tests__/objUtils.spec.ts
@@ -0,0 +1,69 @@
+import { smartMergeArraysWithNameObjects } from '../utils/objUtils';
+
+describe('objUtils', () => {
+  describe('smartMergeArraysWithNameObjects', () => {
+    /** we only use the first two params of the customization utility, so ignore the last 3 */
+    const smartMergeArraysWithNameObjectsWithUsedParams = (v1: any, v2: any) =>
+      smartMergeArraysWithNameObjects(v1, v2, undefined, undefined, undefined);
+
+    it('should do nothing with nulls', () => {
+      expect(smartMergeArraysWithNameObjectsWithUsedParams(null, null)).toBe(undefined);
+    });
+
+    it('should do nothing with objects', () => {
+      expect(
+        smartMergeArraysWithNameObjectsWithUsedParams({ a: true }, { a: false, b: true }),
+      ).toBe(undefined);
+    });
+
+    it('should do nothing with string[]', () => {
+      expect(smartMergeArraysWithNameObjectsWithUsedParams(['test'], ['test2'])).toBe(undefined);
+    });
+
+    it('should do nothing with invalid object arrays', () => {
+      expect(
+        smartMergeArraysWithNameObjectsWithUsedParams([{ id: 'test' }], [{ id: 'test2' }]),
+      ).toBe(undefined);
+    });
+
+    it('should replace 2nd object if given two same correct objects arrays', () => {
+      expect(
+        smartMergeArraysWithNameObjectsWithUsedParams(
+          [{ name: 'test', value: '1' }],
+          [{ name: 'test', value: '2' }],
+        ),
+      ).toEqual([{ name: 'test', value: '2' }]);
+    });
+
+    it('should add 2nd object if given two different correct object arrays', () => {
+      expect(
+        smartMergeArraysWithNameObjectsWithUsedParams(
+          [{ name: 'test', value: '1' }],
+          [{ name: 'test2', value: '2' }],
+        ),
+      ).toEqual([
+        { name: 'test', value: '1' },
+        { name: 'test2', value: '2' },
+      ]);
+    });
+
+    it('should replace and add as appropriate if given two correct object arrays', () => {
+      expect(
+        smartMergeArraysWithNameObjectsWithUsedParams(
+          [
+            { name: 'test', value: '1' },
+            { name: 'test3', value: '3' },
+          ],
+          [
+            { name: 'test', value: '1b' },
+            { name: 'test2', value: '2' },
+          ],
+        ),
+      ).toEqual([
+        { name: 'test', value: '1b' },
+        { name: 'test3', value: '3' },
+        { name: 'test2', value: '2' },
+      ]);
+    });
+  });
+});
diff --git a/backend/src/routes/api/notebooks/utils.ts b/backend/src/routes/api/notebooks/utils.ts
index c4de264e86..b3efc2a3fe 100644
--- a/backend/src/routes/api/notebooks/utils.ts
+++ b/backend/src/routes/api/notebooks/utils.ts
@@ -120,8 +120,8 @@ export const enableNotebook = async (
   const url = request.headers.origin;
 
   try {
-    await getNotebook(fastify, notebookNamespace, name);
-    return await updateNotebook(fastify, username, url, notebookData);
+    const notebook = await getNotebook(fastify, notebookNamespace, name);
+    return await updateNotebook(fastify, username, url, notebookData, notebook);
   } catch (e) {
     if (e.response?.statusCode === 404) {
       return await createNotebook(fastify, username, url, notebookData);
diff --git a/backend/src/types.ts b/backend/src/types.ts
index bde7b3a527..a65214c6d4 100644
--- a/backend/src/types.ts
+++ b/backend/src/types.ts
@@ -766,7 +766,12 @@ export type DetectedAccelerators = {
 
 export type EnvironmentVariable = EitherNotBoth<
   { value: string | number },
-  { valueFrom: Record<string, unknown> }
+  {
+    valueFrom: Record<string, unknown> & {
+      configMapKeyRef?: { key: string; name: string };
+      secretKeyRef?: { key: string; name: string };
+    };
+  }
 > & {
   name: string;
 };
diff --git a/backend/src/utils/notebookUtils.ts b/backend/src/utils/notebookUtils.ts
index ba93cba7aa..319d4851d9 100644
--- a/backend/src/utils/notebookUtils.ts
+++ b/backend/src/utils/notebookUtils.ts
@@ -1,4 +1,5 @@
 import { getDashboardConfig } from './resourceUtils';
+import { mergeWith } from 'lodash';
 import {
   ContainerResourceAttributes,
   EnvironmentVariable,
@@ -30,6 +31,7 @@ import {
 import { DEFAULT_NOTEBOOK_SIZES, DEFAULT_PVC_SIZE, MOUNT_PATH } from './constants';
 import { FastifyRequest } from 'fastify';
 import { verifyEnvVars } from './envUtils';
+import { smartMergeArraysWithNameObjects } from './objUtils';
 import { getImageInfo } from '../routes/api/images/imageUtils';
 
 export const generateNotebookNameFromUsername = (username: string): string =>
@@ -510,6 +512,7 @@ export const updateNotebook = async (
   username: string,
   url: string,
   notebookData: NotebookData,
+  oldNotebook: Notebook,
 ): Promise<Notebook> => {
   if (!notebookData) {
     const error = createCustomError(
@@ -521,7 +524,42 @@ export const updateNotebook = async (
     throw error;
   }
   try {
-    const notebookAssembled = await generateNotebookResources(fastify, username, url, notebookData);
+    const serverNotebook = await generateNotebookResources(fastify, username, url, notebookData);
+
+    // Fix for Workbench Certs that get overridden
+    // We are intentionally applying on some details as to avoid implementing logic to properly
+    // manage the notebook the same way as workbench
+    const importantOldNotebookDetails: RecursivePartial<Notebook> = {
+      spec: {
+        template: {
+          spec: {
+            containers: [
+              {
+                // Drop all env vars we added in the past, because we will just add them back if they are still there
+                env: oldNotebook.spec.template.spec.containers[0].env.filter(({ valueFrom }) => {
+                  if (!valueFrom) {
+                    return true;
+                  } else {
+                    const value = valueFrom.secretKeyRef ?? valueFrom.configMapKeyRef;
+                    return !value?.name?.startsWith('jupyterhub-singleuser-profile');
+                  }
+                }),
+                volumeMounts: oldNotebook.spec.template.spec.containers[0].volumeMounts,
+              },
+            ],
+            volumes: oldNotebook.spec.template.spec.volumes,
+          },
+        },
+      },
+    };
+
+    const notebookAssembled = mergeWith(
+      {},
+      importantOldNotebookDetails,
+      serverNotebook,
+      smartMergeArraysWithNameObjects,
+    );
+
     const response = await fastify.kube.customObjectsApi.patchNamespacedCustomObject(
       'kubeflow.org',
       'v1',
diff --git a/backend/src/utils/objUtils.ts b/backend/src/utils/objUtils.ts
new file mode 100644
index 0000000000..db78e8381b
--- /dev/null
+++ b/backend/src/utils/objUtils.ts
@@ -0,0 +1,30 @@
+import { MergeWithCustomizer } from 'lodash';
+
+/**
+ * When given two object arrays that have "name" keys, replace when keys are the same, or add to
+ * the end when new key.
+ *
+ * Note: returns `undefined` if invalid data is provided.
+ *
+ * @see mergeWith -- lodash mergeWith customizer
+ */
+export const smartMergeArraysWithNameObjects: MergeWithCustomizer = (objValue, srcValue) => {
+  type GoodArray = { name: string }[];
+  const isGoodArray = (v: any): v is GoodArray => Array.isArray(v) && v.length > 0 && v[0].name;
+  if (isGoodArray(objValue) && isGoodArray(srcValue)) {
+    // Arrays with objects that have a .name property, sync on merge for the name
+    return srcValue.reduce<GoodArray>((newArray, elm) => {
+      const key = elm.name;
+      const index = newArray.findIndex(({ name }) => name === key);
+      if (index >= 0) {
+        // existing value, replace
+        newArray[index] = elm;
+      } else {
+        // didn't find existing name, add to end
+        newArray.push(elm);
+      }
+
+      return newArray;
+    }, objValue);
+  }
+};